CN1155539A - Endothelin receptor antagonists - Google Patents

Endothelin receptor antagonists Download PDF

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CN1155539A
CN1155539A CN 96109279 CN96109279A CN1155539A CN 1155539 A CN1155539 A CN 1155539A CN 96109279 CN96109279 CN 96109279 CN 96109279 A CN96109279 A CN 96109279A CN 1155539 A CN1155539 A CN 1155539A
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methoxyphenyl
carboxylic acid
phenyl
methoxy
hydroxyl
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W·密德斯基
M·奥瓦德
D·多斯奇
W·科拉蒂
C·J·施密格斯
M·查里斯塔尔
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Merck Patent GmbH
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Merck Patent GmbH
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Abstract

Novel compounds of the formula I in which -Y-Z-, R1, R2, R3, R4 and R5 have the meanings as stated in the specification, and their salts show endothelin receptor antagonist properties.

Description

Endothelin receptor antagonists
The present invention relates to compound and salt thereof shown in the formula I.
Figure A9610927900061
In the formula-Y-Z-is-NR 7-CO-,-N=C (OR 7)-or-N=CR 8-, R 1Be Ar, R 2Be COOR 6, (CH 2) nCOOR 6, CN, 1H-tetrazolium-5-base or CONHSO 2Ar, R 3, R 4, R 5Be R independently of one another 6, OR 6, S (O) mR 6, Hal, NO 2, NR 6R 6 ', NHCOR 6, NHSO 2R 6, OCOR 6, COR 6, COOR 6Or CN, wherein R 3With R 4Can also form O (CH jointly 2) nThe O base, R 6, R 6 'Be H, C independently of one another 1-6Alkyl, benzyl or phenyl, R 7Be (CH 2) nAr, R 8Be Ar or OAr, Ar is not for replacing or by R 9, R 10Or R 11Replace once, phenyl or the substituted naphthyl or the group of secondary or three times
Figure A9610927900062
This group be not substituted or at its phenyl moiety by R 9Or R 10Replace once or secondary, or group
Figure A9610927900071
This group be not substituted or on its cyclohexadienyl by R 9Or R 10Replace once or secondary R 9, R 10, R 11Be R independently of one another 6, OR 6, Hal, CF 3, OCF 3, OCHF 2, OCH 2F, NO 2, NR 6R 6 ', NHCOR 6, CN, NHSO 2R 6, COOR 6, COR 6, CONHSO 2Ar, O (CH 2) nR 2, O (CH 2) nOR 6Or S (O) mR 6, E is CH 2, S or O, D is carbonyl or (C (R 6R 6 ')) n, X is O or S, and Hal is F, Cl, Br or I, and m is 0,1 or 2, and n is 1,2 or 3.
WO93/08799 has described and has had 1, the similar compound of 2-indane and this structure of indenyl, WO94/14434 has described the similar compound that has the indoles system, and EP0526708A1 has described pyrimidine derivatives, and EP0617001A1 has described phenyl and Haphthyl compounds.
Basis of the present invention has been to find the novel cpd that possesses valuable characteristic, especially can be used to produce medicine.
Have found that Compound I and salt thereof possess very valuable pharmacological characteristic when can being accepted well.Particularly, they present the endothelin receptor antagonists characteristic and therefore are used to treat diseases, such as hypertension, heart failure, coronary heart disease, kidney, brain and myocardial ischaemia, renal insufficiency, big cerebral infarction, subarachnoid hemorrhage, arteriosclerosis, pulmonary hypertension, inflammation, asthma, hyperplasia of prostate, interior toxicogenic shock and use the complication that produces after the material such as S-Neoral, and other and active other the relevant disease of endothelin.
These compounds especially show the inferior acceptor ET of endothelin AAnd ET BHigh-affinity.These effects can by in the conventional body or in vitro method determine that these methods are just like people J.Med.Chem.37 such as P.D.Stein, 1994, people Proc.Natl.Acad.Sci.USA91 such as 329-331 and E.Ohlstein, 1994,8052-8056.
The method of suitable definite antihypertensive effect is just like people J.Cardiovasc Pharmacol.22 such as M.K.Bazil, and 1993, people such as 897-905 and J.Lange, Lab Animal 20,1991, appl.Note 1016.
Compound I can be used as medicine activity component and is used to medical science and animal doctor, is specifically used for preventing and/or treating heart trouble, circulation and vascular disease, especially hypertension and heart failure.
The present invention relates to Compound I and salt thereof, the preparation method of these compounds and salt thereof, it is characterized in that (a) for prepare wherein-Y-Z-is-NR 7-CO-or-N=C (OR 7)-Compound I, R wherein 1, R 2, R 3, R 4And R 5Suc as formula described Compound I I of I and compound R 7-Q (III) reaction Q is the OH base of Cl, Br, I or free or reactive functional modification in formula III, R 7Define suc as formula I, or be (b) for prepare wherein-Y-Z-for-N=C (Ar)-Compound I, compound IV and boron compound V are reacted
Figure A9610927900082
Q is Cl, Br or I in the formula, R 1, R 2, R 3, R 4With R 5Suc as formula the I definition,
L in Ar-BLL ' the V formula, L ' are OH, OCH independently of one another 3, OC 2H 5Or OC 3H 7Ar defines suc as formula I, or be c) for prepare wherein-Y-Z-for-N=C (OAr)-Compound I, making Q wherein is the compound IV and compd A r-OH (VI) reaction of Cl, Br, I or reactive functional modification OH base, and/or is that following manner is with more than one R in the Compound I by way of example 1, R 2, R 3, R 4And/or R 5Groups converted is more than one radicals R 1, R 2, R 3, R 4And/or R 5: being amido with nitroreduction i), is carboxyl with hydrolysis of ester group ii), iii) by the reduction amination effect amino is converted into alkylated amines, iv) carboxyl is converted into the sulfonamido carbonyl, and/or alkali or the acid of formula I is converted into one of its esters.
Group such as R repeatedly appearred in all that 6With the implication of Ar be independent of each other.
In following formula, alkyl has 1-6, preferred 1-4 carbon atom.Alkyl is preferably methyl, also has ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl, also has amyl group, 1-, 2-or 3-methyl butyl, 1,1-or 1 in addition, 2-or 2,2-dimethyl propyl, 1-ethyl propyl, hexyl, 1-, 2-, 3-or 4-methyl amyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3-or 3,3-dimethylbutyl, 1-or 2-ethyl-butyl, 1-ethyl-1-methyl-propyl, 1-ethyl-2-methyl-propyl, 1,1,2-or 1,2,2-trimethylammonium propyl group.E is in particular CH 2Or O, in addition, can also be S.D is in particular carboxyl and CH 2X is preferably O, is preferably S in addition.M is in particular O, is preferably 1 and 2 in addition.N is preferably 1, is preferably 2 or 3 in addition.Hal is preferably F, Cl or Br, but can be I equally.
Ar is not for being substituted; preferably-as mentioned above-phenyl that coverlet replaces; specifically be preferably phenyl; adjacent; between or p-methylphenyl; adjacent; between or to ethylphenyl; adjacent; between or to the propyl group phenyl; adjacent; between or the p-isopropyl phenyl; adjacent; between or to tert-butyl-phenyl; adjacent; between or p-trifluoromethyl phenyl; adjacent; between or p-hydroxybenzene; adjacent; between or p-nitrophenyl; adjacent; between or p-aminophenyl, the neighbour; between or right-(N-methylamino) phenyl, the neighbour; between or to the acetamido phenyl; adjacent; between or right-(trifluoromethoxy) phenyl; adjacent; between or to cyano-phenyl, the neighbour; between or p-methoxyphenyl, the neighbour; between or to ethoxyl phenenyl; adjacent; between or to carboxyl phenyl; adjacent; between paired methoxycarbonyl phenyl, the neighbour; between or to carbethoxy phenyl, the neighbour; between or to the carbobenzoxy-(Cbz) phenyl; adjacent; between or right-(carboxylic methoxy) phenyl; adjacent; between or right-(methoxycarbonyl methoxy) phenyl, the neighbour; between or right-(methoxycarbonyl oxyethyl group) phenyl, the neighbour; between or right-(N; the N dimethylamine base) phenyl; adjacent; between or right-(N-ethylamino-) phenyl, the neighbour; between or right-(N, N dimethylamine base) phenyl; adjacent; between or right-fluorophenyl; adjacent; between or right-bromophenyl, the neighbour; between or rubigan, the neighbour; between or right-(difluoro-methoxy) phenyl; adjacent; between or right-(fluorine methoxyl group) phenyl; adjacent; between or to formyl radical phenyl, neighbour; between or to acetylphenyl, the neighbour; between or to the propionyl phenyl; adjacent; between or to the butyryl radicals phenyl; adjacent; between or to pentanoyl phenyl, neighbour; between or right-(phenyl sulfonamido carbonyl) phenyl, the neighbour; between or to Phenoxyphenyl; adjacent; between or to the methylbenzene sulfenyl; adjacent; between or to methyl sulfinyl phenyl, neighbour; between or to sulfonyloxy methyl phenyl, neighbour; between or to benzyl oxy phenyl; adjacent; between or to the cyano group methoxyphenyl; in addition, preferred 2, the 3-methylenedioxyphenyl; 3; the 4-methylenedioxyphenyl, 2,3-ethylenedioxy phenyl; 3; 4-ethylenedioxy phenyl, 6-chloro-3,4-methylene dioxy phenyl group; 2; 3-(2-oxo-methylene-dioxy) phenyl, 2,3-; 2; 4-, 2,5-; 2; 6-, 3,4-; or 3; 5-(difluoro-methoxy) (carboxyl methoxyl group) phenyl, 2,3-; 2; 4-, 2,5-; 2; 6-, 3,4-or 3; 5-methoxyl group (carboxyl methoxyl group) phenyl; 2,3-, 2; 4-; 2,5-, 2; 6-; 3,4-or 3,5-hydroxyl (carboxyl methoxyl group) phenyl.
In addition, Ar is preferably 2, the 3-dihydro benzo furyl, 2,3-dihydro-2-oxygen furyl, 1,3-dithio-2,3-indanyl, 2,1,3-diazosulfide-4 or 5-base, 2,1,3-benzo oxadiazoles-4 or 5-base, in addition, be preferably 2,3-, 2,4-, 2,5-, 2,6-, 3,4-or 3, the 5-difluorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3, the 5-dichlorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-or 3,5-dibromo phenyl, 2-chloro-3-methyl-, 2-chloro-4-methyl-, 2-chloro-5-methyl-, 2-chloro-6-methyl, 2-methyl-3-chlorine, 2-methyl-4-chlorine, the 2-methyl-5-chloro, 2-methyl-6-chlorine, 3-chloro-4-methyl, 3-chloro-5-methyl, or 3-methyl-4-chloro-phenyl-, 2-bromo-3-methyl-, 2-bromo-4-methyl-, 2-bromo-5-methyl, 2-bromo-6-methyl, 2-methyl-3-bromo-, 2-methyl-4-bromine, 2-methyl-5-bromine, 2-methyl-6-bromine, 3-bromo-4-methyl-, 3-bromo-5-methyl-or 3-methyl-4-bromophenyl, 2,4-or 2, the 5-dinitrophenyl, 2,5-or 3,4-dimethoxy phenyl, 3-nitro-4-chloro-phenyl-, 2-amino-3-chloro-, 2-amino-4-chloro-, 2-amino-5-chloro-or 2-amino-6-chloro-phenyl-, 2-nitro-4-N, the N-dimethyl amido-or 3-nitro-4-N, N dimethylamine base phenyl, 3-carboxyl-2-methoxyl group-, 3-carboxyl-4-methoxyl group-or 3-carboxyl-5-methoxyphenyl, 2,3,4-, 2,3,5-, 2,3,6-, 2,4,6-or 3,4, the 5-trichlorophenyl, 2,4,6-tri-tert phenyl, in addition, preferred 2-nitro-4-(trifluoromethyl) phenyl in addition, 3,5-two (trifluoromethyl) phenyl, 2, the 5-xylyl, 2-hydroxyl-3,5-dichlorophenyl, 2-fluoro-5-or 4-fluoro-3-(trifluoromethyl) phenyl, 4-chloro-2-or 4-chloro-3-(trifluoromethyl)-, 2-chloro-4-or 2-chloro-5-(trifluoromethyl) phenyl, 4-bromo-2-or 4-bromo-3-(trifluoromethyl) phenyl are to iodophenyl, 2-nitro-4-p-methoxy-phenyl, 2,5-dimethoxy-4 '-nitrophenyl, 3,5-dicarboxyl phenyl, 2-chloro-3-nitro-5-carboxyl phenyl, 4-chloro-3-carboxyl phenyl, 2-methyl-5-nitro phenyl, 2,4-dimethyl-3-nitrophenyl, 3,6-two chloro-4-aminophenyls, 4-fluoro-3-chloro-phenyl-, 4-fluoro-3,5-3,5-dimethylphenyl, 2-fluoro-4-bromophenyl, 2,5-two fluoro-4-bromophenyls, 2,4-two chloro-5-aminomethyl phenyls, 3-bromo-6-p-methoxy-phenyl, 3-chloro-6-p-methoxy-phenyl, 3-chloro-4-acetylamino phenyl, 4-hydroxyl-3-carboxyl phenyl, 2-methoxyl group-5-tolyl or 2,4,6-triisopropyl phenyl also has naphthyl in addition.
Radicals R 2Be preferably methoxycarbonyl, ethoxycarbonyl, propyl ester base, butyl ester base, carbobenzoxy, also have cyano group, 1H-tetrazolium-5-base or phenyl sulfonyl-amino-carbnyl in addition, still particularly preferred is carboxyl and carboxymethyl.
Radicals R 3, R 4And R 5Be preferably H independently of one another; methyl; ethyl; propyl group; sec.-propyl; butyl; isobutyl-; the sec-butyl or the tertiary butyl; benzyl; F; Cl; Br; methoxyl group; oxyethyl group; phenoxy group; benzyloxy; nitro or cyano group are preferably amino in addition; methylamino; dimethylin; ethylamino-; diethylin; kharophen; propionamido; butyrylamino; methanesulfonamido; ethanesulfonamido; benzene sulfonamido; the methyl ketonic oxygen; the ethyl ketonic oxygen; phenylcarbonyl group oxygen; methoxycarbonyl; ethoxycarbonyl; methylthio group; ethylmercapto group; the rosickyite base; methylsulfinyl; the ethyl sulfinyl; the phenyl sulfinyl; methyl sulphonyl; ethylsulfonyl or phenyl sulfonyl.
Compound I can have an above chiral centre, thereby is different stereoisomeric forms in any ratio.Formula I comprises all these forms.
Therefore, the present invention relates to particularly wherein that at least one described group has the Compound I of one of above-mentioned preferred definition.Some preferred group of compound can represent that wherein the group that does not limit is described suc as formula I with the following formula Ia-Ig corresponding with formula I, but wherein Ia:-Y-Z-is-NR 7-CO-or-N=C (OR 7)-; Ib:-Y-Z-is-N=CR 8-; Ic:-Y-Z-is-NR 7-CO-, R 2Be COOH; Id:-Y-Z-is-NR 7-CO-, Ar are group Ie:-Y-Z-is-N=CR 8, R 8Be Ar, Ar is by R 9, R 10Or R 11Replace once, the phenyl of secondary or three times; If:-Y-Z-is-NR 7-CO-, R 7Be CH 2Ar, Ar are group Ig:-Y-Z-is-N=CR 8-, R 8Be OAr, Ar is a group In addition, as document (Houben-Weyl for example, Methoden der organischenChemie, Georg-Thieme-Verlag, Stuttgart; Especially WO94/14434) described, prepare Compound I and raw material thereof known being suitable under the concrete reaction conditions by currently known methods.Moreover, can also adopt alternative known but that do not describe in detail at this paper.
In case of necessity, can also prepare raw material on the spot, thereby avoid them and reaction mixture separation steps, directly it further is converted into Compound I.
Can preferably, Compound I I and compound III prepare Compound I by being reacted.
In compound III, Q is preferably the OH base of Cl, Br, I or reactive modification as C 1-6Alkylsulfonyloxy (preferred mesyloxy) or C 6-10Aryl-sulfonyl oxygen (preferred phenyl or p-methylphenyl sulfonyloxy).
This reaction usually in inert solvent at acid adhesive, preferably the another kind of salt of basic metal or alkaline earth metal hydroxides, carbonate or supercarbonate or a kind of faintly acid carries out under existing, above-mentioned metal is good with potassium, sodium, calcium or caesium, and adding organic bases alkyl derivative shown in acid amides component or the formula III shown in triethylamine, xylidene(s), pyridine or quinoline or excessive formula II is the useful practice equally.Reaction times is depended on used condition, and between several minutes to 14 days, temperature of reaction is about 0-150 ℃, is generally 20-130 ℃.
Suitable inert solvent be embodied as hydrocarbon such as hexane, sherwood oil, benzene, toluene or dimethylbenzene; Chlorinated hydrocarbon such as trieline, 1,2-ethylene dichloride, tetracol phenixin, chloroform or methylene dichloride; Alcohols such as methyl alcohol, ethanol, Virahol, n-propyl alcohol, propyl carbinol or the trimethyl carbinol; Ethers such as ether, isopropyl ether, tetrahydrofuran (THF) or dioxan; Glycol ethers such as glycol monomethyl first or single ether (methyl glycol or ethyl glycol), glycol dimethyl ether, ketone such as acetone or butanone; Acid amides such as ethanamide, N,N-DIMETHYLACETAMIDE or dimethyl formamide (DMF); Nitrile such as acetonitrile; Sulfoxide such as dimethyl sulfoxide (DMSO) (DMSO); Dithiocarbonic anhydride; Carboxylic acid such as formic acid or acetate; Nitro-compound such as Nitromethane 99Min. or oil of mirbane; The mixture of ester class such as ethyl acetate or these solvents.
Raw material II is novel cpd normally.Yet they can prepare by currently known methods.Like this; for instance; can by cyclisation in the presence of inert solvent and alkali at 1-amino-2-(3; 4-methylene-dioxy benzoyl)-intermediate that generates in 4-phenetole and the chloroformyl methyl acetate reaction process prepares 4-(1; 3-benzo dioxole-5-yl)-1,2-dihydro-2-oxygen quinoline-3-carboxylic acid methyl esters.This process is preferably carried out under about 200 ℃ of 0-; With 30-80 ℃ is good.
Suitable inert solvent and alkali are as mentioned above.
In addition, Compound I can be preferably by obtaining compound IV and V reaction.
In compound IV, Q is preferably Cl or Br, can also be I.
In compound V, L and L ' preferably are OH, methoxyl group, oxyethyl group, propoxy-or isopropoxy independently of one another.
This reaction is carried out in the presence of alkali and noble metal catalyst in inert solvent usually.Reaction times is depended on used condition between several minutes and 14 days, and temperature of reaction is about 0-150 ℃, is generally 20-130 ℃.
Suitable inert solvent and alkali are as mentioned above.
Particularly preferred noble metal catalyst is palladium (O) catalyzer such as tetrakis triphenylphosphine palladium (O).
Raw material IV is novel cpd normally.Yet they can prepare by currently known methods.For instance, can be by 1,2-dihydro-4-(4-p-methoxy-phenyl)-2-oxygen quinoline-3-carboxylic acid methyl esters and POCl 3Preparation 2-chloro-4-(4-methoxyphenyl) quinoline-3-carboxylic acid methyl esters.This reaction is preferably carried out under about 200 ℃ of 0-, is good with 30-80 ℃.
In addition, preferably, can prepare Compound I by compound IV and VI are reacted.
In compound IV, Q is preferably Cl, Br, I or reaction modifying OH base.
Reaction is carried out under the condition of adding a kind of above-mentioned alkali in inert solvent usually.
In addition, can also pass through one or more radicals R 1, R 2, R 3, R 4With/R 5Be converted into one or more other radicals R 1, R 2, R 3, R 4With/R 5And Compound I is converted into another kind of Compound I, for example by in inert solvent such as methyl alcohol or ethanol, reducing nitro, for example by hydrogenation on Raney nickel or Pd/ carbon obtain amido and/or with ester group be converted into carboxyl and/or by the reduction amination effect with amido be converted into alkylated amines and/or by with alcohol reaction esterifying carboxyl group.
In addition, free amine group can be in a conventional manner by acyl chlorides or anhydride acylation or do not replaced or replace the haloalkane alkylation, preferably under-60-+30 ℃, carry out at inert solvent such as methylene dichloride or THF and/or in alkali such as triethylamine or pyridine.
Necessary, can be by ordinary method by functional modified amino and/or hydroxyl in solvolysis or the hydrogenolysis release Compound I.For instance, contain NHCOR 6Or COOR 6The Compound I of base can be converted into and contain NH 2Or the corresponding compounds I of HOOC group.For instance, can be with NaOH or KOH (in Yu Shui, water/THF or the water/dioxan) in 0-100 ℃ of hydrolysis COOR 6Group.
Alkali shown in the formula I can for instance, be converted into relevant acid addition salt by making equivalent alkali react to evaporate subsequently with equivalent acid with acid in inert solvent such as ethanol.The acid that is specially adapted to this reaction can provide physiology pieceable salt.Therefore, can adopt mineral acid such as sulfuric acid, nitric acid, haloid acid example hydrochloric acid or Hydrogen bromide, phosphoric acid such as ortho-phosphoric acid, thionamic acid, also has organic acid, especially lipid acid in addition, alicyclic acid, aryl fatty acid, aromatics or heterocycle list or polycarboxylic acid, sulfonic acid or sulfuric acid such as formic acid, acetate, propionic acid, PIVALIC ACID CRUDE (25), diethylacetic acid, propanedioic acid, succsinic acid, pimelic acid, fumaric acid, toxilic acid, lactic acid, tartrate, oxysuccinic acid, citric acid, glyconic acid, xitix, nicotinic acid, Yi Yansuan, first or ethyl sulfonic acid, ethionic acid, the 2-ethylenehydrinsulfonic acid, Phenylsulfonic acid, tosic acid, naphthene sulfonic acid and naphthalene disulfonic acid, lauryl sulfate.For example can be used to separate and/or purifying compounds I with the salt that physilogically acceptable acid forms as if the flavor hydrochlorate.
In addition, can Compound I be converted into corresponding metal, particularly basic metal or alkaline earth salt or corresponding ammonium salt with alkali (for example sodium hydroxide or potassium or yellow soda ash or potassium).
The invention still further relates to Compound I and/or its physiological acceptable salt and pass through particularly the purposes of method pharmaceutical compositions non-chemically.For this reason, they can with at least a solid, liquid and/or semiliquid carrier or auxiliary agent and, where necessary, be converted into suitable dosage forms with more than one other active substance combination.
In addition, the present invention relates to contain the pharmaceutical composition of at least a Compound I and/or a kind of its physiologically acceptable salt.
These compositions can be used as medicine and are used to medical science or animal doctor.Suitable vehicle for be applicable to enteron aisle (as oral), parenteral or topical and not with the organic or inorganic material of novel cpd reaction, for example water, vegetables oil, benzylalcohol, aklylene glycol, polyoxyethylene glycol, thriacetic acid glycerine ester, gelatin, carbohydrate such as lactose or starch, Magnesium Stearate, talcum, vaseline.Be used to oral specific examples just like tablet, pill, coated tablet, capsule, pulvis, granula, syrup, solution or drops, the suppository that has that is used for rectal administration, the solution that has that is used for parenterai administration, with the oily or the aqueous solution is good, also have suspension, emulsion or implant in addition, what be used for topical has paste, missible oil or a pulvis.All right freezing this class novel cpd, resulting lyophilize product for instance, can be used to produce the injection product.Described composition can be through disinfecting and/or containing auxiliary agent such as lubricant, sanitas, stablizer and/or wetting agent, emulsifying agent, is used to influence salt, buffer substance, tinting material, sweetener and/or several other active substances of osmotic pressure, more than one VITAMIN for example.
Compound I and physiologically acceptable salt thereof can be used to control disease disease, especially hypertension and heart failure.
This causes material of the present invention preferably to be used with about 1-500mg, the particularly quantity of 5-100mg/ dose unit usually.Per daily dose is preferably in about 0.02-10mg/kg body weight.Yet, every patient's concrete dosage depends on multiple factor, the severity of the activity of for example used particular compound, age, body weight, general health, sex, recipe, administration time and approach, discharge rate, medicinal substance combination and concrete illness to be treated.With oral administration is good.
Hereinafter " common operation " means: in case of necessity, add entry, in case of necessity, according to the formation of purpose product with pH regulator to 2-10, by ethyl acetate or CH 2Cl 2Extract, isolate organic phase,, purify, separate required isomer and/or pass through crystallization and purification in the enterprising circumstances in which people get things ready for a trip spectrum of silica gel with dried over sodium sulfate and evaporation.R fValue (on the silica gel); Moving phase: ethyl acetate/methanol 9: 1.Mass spectrum: E1 (electron impact ionization): M +
FAB (high velocity electron bombardment): (M+H) +
Embodiment 1
Restrain 2-methoxybenzyl chlorine (" A ") in CH with 0.4 2Cl 2In 50% solution add by 0.17g salt of wormwood and be in 0.4g4-(1 among the 5mlDMF; 3-benzo dioxole-5-yl)-1; 2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters (obtains by following manner: make 1-amino-2-(3,4-methylene-dioxy benzoyl)-4-phenetole and be in CH 2Cl 2And the chloroformyl methyl acetate in ethyl diisopropylamine reaction, this intermediate of cyclisation in sodium methoxide solution subsequently, m.p.224-225 ℃; 1-amino-2-(3; 4-methylene-dioxy benzoyl)-the 4-phenetole is by making 3; 4-methylene dioxo group benzaldehyde and N-(tertbutyloxycarbonyl)-p-Phenetidine reacts (m.p.113-114 ℃; THF; tert-butyl lithium;-78 ℃), with resulting 3 ', the 4 '-methylene-dioxy of rear oxidation-2-(N-tertbutyloxycarbonyl amido)-5-ethoxy diphenyl base methyl alcohol and remove that amino protecting group obtains, in solution EI-MS285).Stirred reaction mixture 4 hours and carry out routine operation.Obtain N-alkylate 4-(1 like this, 3-benzo dioxole-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid methyl esters, m.p.182-183 ℃ and O-alkylate 4-(1,3-benzo dioxole-5-yl)-and 6-ethoxy-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, m.p.157-158 ℃.
Similarly, by T wherein is the 4-p-methoxy-phenyl, 2, the 4-Dimethoxyphenyl, 2-benzyloxy-4-p-methoxy-phenyl, 2-hydroxyl-4-p-methoxy-phenyl, 2-carboxyl methoxyl group-4-p-methoxy-phenyl, the 4-T-1 of 2-hydroxyl-oxethyl-4-p-methoxy-phenyl, 2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters obtains wherein with " A ", and T is the 4-p-methoxy-phenyl, 2, the 4-Dimethoxyphenyl, 2-benzyloxy-4-p-methoxy-phenyl, 2-hydroxyl-4-p-methoxy-phenyl, 2-carboxyl methoxyl group-4-p-methoxy-phenyl, the 4-T-1 of 2-hydroxyl-oxethyl-4-p-methoxy-phenyl, 2-dihydro-6-oxyethyl group-1-(2-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid methyl esters and wherein T be the 4-p-methoxy-phenyl, 2, the 4-Dimethoxyphenyl, 2-benzyloxy-4-p-methoxy-phenyl, 2-hydroxyl-4-p-methoxy-phenyl, 2-carboxyl methoxyl group-4-p-methoxy-phenyl, 4-T-6-oxyethyl group-the 2-of 2-hydroxyl-oxethyl-4-p-methoxy-phenyl (2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters.
Similarly, make 3-methoxybenzyl chlorine and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(3-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.138-139 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(3-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.139-140 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 4-methoxybenzyl chlorine and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(4-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.157-158 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(4-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.141-142 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.177-178 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl
Similarly, make 6-chloro-3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(6-chloro-3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.207-208 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(6-chloro-3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.200-201 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make benzyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-benzyl-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-benzyl-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2-(methylthio group) benzyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(2-methylthio group benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(2-methylthio group benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2-methyl sulfinyl benzyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(2-methyl sulfinyl benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(2-methyl sulfinyl benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 2-methyl sulphonyl benzyl chloride and 4-T-1; 2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-oxyethyl group-1-(2-methyl sulphonyl benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(2-methyl sulphonyl benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,3-veratryl chlorine and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(2, the 3-veratryl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.180-181 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(2,3-dimethoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.133-134 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,3-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(2,3-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(2,3-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,1,3-diazosulfide-5-methyl chloride and 4-T-1,2-dihydro-6-oxyethyl group-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-oxyethyl group-1-(2,1,3-diazosulfide-5-methyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-oxyethyl group-2-(2,1,3-diazosulfide-5-methyl oxygen) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, by " A " and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.178-179 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3-methoxybenzyl chlorine and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(3-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.162-163 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(3-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 4-methoxybenzyl chlorine and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(4-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.214-215 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(4-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.192-193 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 6-chloro-3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(6-chloro-3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(6-chloro-3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make benzyl chloride and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-benzyl-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base, m.p.139-140 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-benzyloxy quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2-methylthio group benzyl chloride and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(2-methylthio group benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2-methylthio group benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 2-methylsulfinyl benzyl chloride and 4-T-1; 2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-1-(2-methylsulfinyl benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2-methylsulfinyl benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 2-methyl sulphonyl benzyl chloride and 4-T-1; 2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-1-(2-methylsulfonyl benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2-methylsulfonyl benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,3-veratryl chlorine and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(2, the 3-veratryl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2,3-dimethoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,3-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-2-oxoquinoline-3-carboxylate methyl ester reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(2,3-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2,3-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; by " A " and 4-T-1; 2-dihydro-6-propionyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-propionyl-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-propionyl-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 3-methoxybenzyl chlorine and 4-T-1; 2-dihydro-6-propionyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-propionyl-1-(3-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-propionyl-2-(3-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 4-methoxybenzyl chlorine and 4-T-1; 2-dihydro-6-propionyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-propionyl-1-(4-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-propionyl-2-(4-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 3; 4-(methylenedioxy) benzyl chloride and 4-T-1; 2-dihydro-6-propionyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-propionyl-1-(3; 4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-propionyl-2-(3; 4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make 6-chloro-3; 4-(methylenedioxy) benzyl chloride and 4-T-1; 2-dihydro-6-propionyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-propionyl-1-(6-chloro-3; 4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-propionyl-2-(6-chloro-3; 4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly; make benzyl chloride and 4-T-1; 2-dihydro-6-propionyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1; 2-dihydro-6-propionyl-1-benzyl-2-Oxoquinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2; 4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-propionyl-2-benzyloxy quinoline-3-carboxylic acid methyl esters; wherein T is 1; 3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, by " A " and 4-T-1,2-dihydro-6,7-dimethoxy-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethoxy-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethoxy-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3-methoxybenzyl chlorine and 4-T-1,2-dihydro-6,7-dimethoxy-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethoxy-1-(3-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethoxy-2-(3-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 4-methoxybenzyl chlorine and 4-T-1,2-dihydro-6,7-dimethoxy-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethoxy-1-(4-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethoxy-2-(4-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6,7-dimethoxy-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethoxy-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethoxy-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 6-chloro-3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6,7-dimethoxy-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethoxy-1-(6-chloro-3,4-(methylenedioxy) oxygen benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethoxy-2-(6-chloro-3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make benzyl chloride and 4-T-1,2-dihydro-6,7-dimethoxy-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethoxy-1-benzyl-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethoxy-2-benzyloxy quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, by " A " and 4-T-1,2-dihydro-6,7-dimethyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethyl-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethyl-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3-methoxybenzyl chlorine and 4-T-1,2-dihydro-6,7-dimethyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethyl-1-(3-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethyl-2-(3-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 4-methoxybenzyl chlorine and 4-T-1,2-dihydro-6,7-dimethyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethyl-1-(4-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethyl-2-(4-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6,7-dimethyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethyl-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethyl-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 6-chloro-3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6,7-dimethyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethyl-1-(6-chloro-3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethyl-2-(6-chloro-3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make benzyl chloride and 4-T-1,2-dihydro-6,7-dimethyl-2-Oxoquinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6,7-dimethyl-1-benzyl-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6,7-dimethyl-2-benzyloxy quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, by " A " and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3-methoxybenzyl chlorine and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(3-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(3-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 4-methoxybenzyl chlorine and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(4-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(4-methoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 6-chloro-3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(6-chloro-3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(6-chloro-3,4-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-benzyl-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-benzyloxy quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2-methylthio group benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(2-methylthio group benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(2-methylthio group benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2-methylsulfinyl benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(2-methylsulfinyl benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(2-methylsulfinyl benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2-methylsulfonyl benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(2-methylsulfonyl benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(2-methylsulfonyl benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,3-veratryl chlorine and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(2, the 3-veratryl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(2,3-dimethoxy benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 2,3-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-6-ethyl-2-oxo quinoline-3-carboxylic acid methyl esters reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-6-ethyl-1-(2,3-(methylenedioxy) benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-6-ethyl-2-(2,3-(methylenedioxy) benzyloxy) quinoline-3-carboxylic acid methyl esters, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Embodiment 2
With 0.5g4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-oxyethyl group-1-(2-methoxybenzyl)-2-oxidation quinoline-3-carboxylic acid methyl esters and the 6ml 5NKOH solution in 10ml methyl alcohol refluxes and boiled 2 hours, obtain 4-(1 through behind the routine operation, 3-benzo dioxole-5-yl)-1,2-dihydro-6-ethoxy-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid, m.p.225-226 ℃.Similarly, by 4-(1,3-benzo dioxole-5-yl)-6-oxyethyl group-2-(2-methoxyl group benzyloxy base) quinoline-3-carboxylic acid methyl esters obtains O-alkylate 4-(1,3-benzo dioxole-5-yl)-6-oxyethyl group-2-(2-methoxy benzyloxy) quinoline-3-carboxylic acid.
Similarly, where T is the 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl The 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - methoxy-benzyl) - 2 - oxo-quinoline-3 - carboxylate and 4-T-6-ethoxy-2 - (2 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl Ester And wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl The 4-T-1, 2 - dihydro-6 - ethoxy-1 - (3 - methoxy-benzyl) - - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (4 - methoxy-benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (3,4 - methylenedioxy Benzyl)-2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (3,4 - methylenedioxy benzyloxy) quinolin-3 - Carboxylate 4-T-1, 2 - dihydro-6 - ethoxy-1 - (6 - chloro-3 ,4 - 2nd Methylenedioxy-benzyl)-2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (6 - chloro-3 ,4 - (methylenedioxy) benzyloxy) quinoline -3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - benzyl-2 - oxoquinoline-3 - Carboxylate 4-T-6-ethoxy-2 - benzyloxy-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - (methylthio) benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (2 - (methylthio) benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - methylsulfinyl-benzyl) -2 - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (2 - methylsulfinyl benzyloxy)-quinoline-3 - carboxylic Methyl ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - methanesulfonyl benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (2 - methanesulfonyl-benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2,3 - dimethoxybenzyl) -2 - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (2,3 - dimethoxy-benzyloxy)-quinoline-3 - Carboxylate 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2,3 - methylenedioxy Benzyl)-2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (2,3 - methylenedioxy benzyloxy) quinoline - 3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2,1,3 - benzothiazole Oxadiazol-5 - methyl) -2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethoxy-2 - (2,1,3 - thiadiazol-5-benzo - methoxy- Yl) quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2 - methoxy-benzyl)-2 - oxoquinoline-3 - Carboxylate 4-T-2-(2 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (3 - methoxy-benzyl)-2 - oxoquinoline-3 - Carboxylate 4-T-2-(3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (4 - methoxy-benzyl)-2 - oxoquinoline-3 - Carboxylate 4-T-2-(4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (3,4 - methylenedioxy benzyl) -2 - Oxygen quinoline-3 - carboxylic acid methyl ester, 4-T-2-(3,4 - methylenedioxy benzyloxy) quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (6 - chloro -3,4 - methylenedioxy benzyl) -2 - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-2-(6 - chloro-3 ,4 - (methylenedioxy) benzyloxy) quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro -1-1 - benzyl-2 - oxoquinoline-3 - carboxylic acid methyl Esters, 4-T-2-benzyloxy-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2 - (methylthio) benzyl)-2 - oxoquinoline-3 - Carboxylate 4-T-2-(2 - methylthio-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2 - methylsulfinyl benzyl)-2 - oxide quinoline -3 - carboxylic acid methyl ester, 4-T-2-(2 - methylsulfinyl benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2 - methanesulfonyl benzyl)-2 - oxoquinoline-3 - Carboxylate 4-T-2-(2 - methanesulfonyl-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2,3 - dimethoxybenzyl) -2 - Oxygen quinoline -3 - carboxylic acid methyl ester, 4-T-2-(2,3 - dimethoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2,3 - methylenedioxy benzyl) -2 - Oxygen quinoline-3 - carboxylic acid methyl ester, 4-T-2-(2,3 - methylenedioxy benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2,1,3 - thiadiazol-5-benzo - A Yl) -2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-2-(2,1,3 - benzo-thiadiazol-5 - methoxy)-quinoline-3- - Carboxylate 4-T-1, 2 - dihydro-1 - (2 - methoxy-benzyl) -6 - propanoyl -2 - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-2-(2 - methoxy-benzyloxy)-6 - propionyl-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - propanoyl -1 - (3 - methoxy-benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-propionyl-2 - (3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - propanoyl -1 - (4 - methoxy-benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-propionyl-2 - (4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - propanoyl -1 - (3,4 - methylenedioxy Benzyl)-2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-propionyl-2 - (3,4 - methylenedioxy benzyloxy) quinolin-3 - Carboxylate 4-T-1, 2 - dihydro-6 - propanoyl -1 - (6 - chloro-3 ,4 - 2nd Methylenedioxy-benzyl)-2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-propionyl-2 - (6 - chloro-3 ,4 - (methylenedioxy) benzyloxy) quinoline -3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - propionyl -1 - benzyl-2 - oxoquinoline-3 - Carboxylate 4-T-6-propionyl-2 - benzyloxy-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (2 - (methylthio) benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2 - (methylthio) benzyloxy)-quinoline-3 - carboxylic acid methyl Esters, 4-T-1, 2 - dihydro-6 - ethyl-1 - (2 - methylsulfinyl-benzyl) -2 - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2 - methylsulfinyl benzyloxy)-quinoline-3 - carboxylic acid Ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (2 - methanesulfonyl benzyl) - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2 - methanesulfonyl-benzyloxy)-quinoline-3 - carboxylic acid methyl Esters, 4-T-1, 2 - dihydro-6 - ethyl-1 - (2,3 - dimethoxybenzyl) -2 - Oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2,3 - dimethoxy-benzyloxy)-quinoline-3 - carboxylic Methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (2,3 - methylenedioxy benzyl Yl) -2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2,3 - methylenedioxy benzyloxy) quinolin-3 - Carboxylate 4-T-1, 2 - dihydro-6 - ethyl-1 - (2,1,3 - thiadiazole benzo -5 - methyl) -2 - oxoquinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2,1,3 - thiadiazol-5-benzo - methoxy) Quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (2 - methoxy-benzyl) -6,7 - dimethoxy- -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-2-(2 - methoxy-benzyloxy) -6,7 - dimethoxy-quinoline-3 - Carboxylate 4-T-1, 2 - dihydro-1 - (3 - methoxy-benzyl) -6,7 - dimethoxy- -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-2-(3 - methoxy-benzyloxy) -6,7 - dimethoxy-quinoline-3 - Carboxylate 4-T-1, 2 - dihydro-1 - (4 - methoxybenzyl) -6,7 - dimethoxy- -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-2-(4 - methoxy-benzyloxy) -6,7 - dimethoxy-quinoline-3 - Carboxylate 4-T-1, 2 - dihydro-1 - (3,4 - methylenedioxy benzyl) -6,7 - Dimethoxy-2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-2-(3,4 - methylenedioxy benzyloxy) -6,7 - dimethoxy- Quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - (6 - chloro -3,4 - methylenedioxy benzyl) -6,7 - Dimethoxy-2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-2-(6 - chloro -3,4 - methylenedioxy-benzyloxy) -6,7 - Dimethoxy-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-1 - benzyl-6 ,7 - dimethoxy-2 - oxo- Quinoline-3 - carboxylic acid methyl ester, 4-T-2-benzyloxy-6 ,7 - dimethoxy-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (2 - methoxy-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6, 7 - dimethyl-2 - (2 - methoxy-benzyloxy)-quinoline-3 - carboxylic Methyl ester, 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (3 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6, 7 - dimethyl-2 - (3 - methoxy-benzyloxy)-quinoline-3 - carboxylic Methyl ester, 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (4 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6, 7 - dimethyl-2 - (4 - methoxy-benzyloxy)-quinoline-3 - carboxylic Methyl ester, 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (3,4 - methylenedioxy Benzyl) -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6, 7 - dimethyl-2 - (3,4 - methylenedioxy-benzyloxy)-quinoline -3 - Carboxylate, 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (6 - chloro-3 ,4 - Methylenedioxy benzyl) -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6, 7 - dimethyl-2 - (6 - chloro-3 ,4 - (methylenedioxy) benzyloxy Yl) quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - benzyl-2 - oxo-quinoline -3 - carboxylic acid methyl ester, 4-T-2-benzyloxy-6 ,7 - dimethoxy-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (2 - methoxy-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (2 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (3 - methoxy-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (4 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - (3,4 - methylenedioxy benzyl Yl) -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (3,4 - methylenedioxy-benzyloxy)-quinoline-3 - Carboxylate 4-T-1, 2 - dihydro-6 - ethyl-1 - (6 - chloro-3 ,4 - methylene Dioxy benzyl) -2 - oxo-quinoline-3 - carboxylic acid methyl ester, 4-T-6-ethyl-2 - (6 - chloro-3 ,4 - (methylenedioxy) benzyloxy)-quinoline -3 - carboxylic acid methyl ester, 4-T-1, 2 - dihydro-6 - ethyl-1 - benzyl-2 - oxo-quinoline-3- - Carboxylate 4-T-2-benzyloxy-6 - ethyl-quinoline-3 - carboxylic acid methyl ester, Get 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - methoxy-benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 4 - methoxyphenyl, m.p.234.5 ℃ 2,4 - dimethoxyphenyl, m.p.220-221 ℃ 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (3 - methoxy-benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp174-175 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl, mp53-54 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (4 - methoxy-benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp209-210 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (3,4 - (methylenedioxy) benzyl Yl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp210-211 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (3,4 - methylenedioxy benzyloxy) quinoline - 3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (6 - chloro-3 ,4 - 2nd Methylenedioxy-benzyl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp247-248 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (6 - chloro -3,4 - methylenedioxy benzyloxy) Quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - benzyl-2 - oxo-quinoline-3- - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - benzyloxy-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - (methylthio) benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2 - (methylthio) benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - methylsulfinyl-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2 - methylsulfinyl benzyloxy)-quinolin-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2 - methanesulfonyl benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2 - methanesulfonyl-benzyloxy)-quinoline-3 - carboxylic Acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2,3 - dimethoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2,3 - dimethoxy-benzyloxy)-quinolin-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2,3 - dimethoxyphenyl methylene Benzyl)-2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2,3 - methylenedioxy benzyloxy) quinoline - 3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethoxy-1 - (2,1,3 - benzothiazole Oxadiazol-5 - methyl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-ethoxy-2 - (2,1,3 - thiadiazol-5-benzo - methoxy- Yl) quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2 - methoxy-benzyl) -2 - oxo-quinoline-3- - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp231-232 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (3 - methoxy-benzyl) -2 - oxo-quinoline-3- - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp162-163 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (4 - methoxy-benzyl) -2 - oxo-quinoline-3- - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp222-223 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (3,4 - (methylenedioxy) benzyl)-2 - oxide Substituting quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp216-217 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(3,4 - methylenedioxy benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (6 - chloro-3 ,4 - (methylenedioxy) benzyl group) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(6 - chloro -3,4 - methylenedioxy-benzyloxy)-quinoline-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - benzyl-2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl, mp184-185 ℃ 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-benzyloxy-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2 - (methylthio) benzyl)-2 - oxo-quinoline -3 - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2 - methylthio-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2 - methylsulfinyl benzyl)-2 - oxo- Quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2 - methylsulfinyl benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2 - methanesulfonyl benzyl) -2 - oxo-quinoline -3 - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2 - methanesulfonyl-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2,3 - dimethoxybenzyl) -2 - oxo- Quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2,3 - dimethoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2,3 - (methylenedioxy) benzyl)-2 - oxide Substituting quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2,3 - methylenedioxy benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-1 - (2,1,3 - thiadiazol-5-benzo - A Yl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-2-(2,1,3 - benzo-thiadiazol-5 - methoxy)-quinoline-3- - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - propanoyl -1 - (2 - methoxy-benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-propionyl-2 - (2 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - propanoyl -1 - (3 - methoxy-benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-propionyl-2 - (3 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - propanoyl -1 - (4 - methoxy-benzyl) - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-propionyl-2 - (4 - methoxy-benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - propanoyl -1 - (3,4 - (methylenedioxy) benzyl Yl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-propionyl-2 - (3,4 - methylenedioxy benzyloxy) quinoline - 3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - propanoyl -1 - (6 - chloro-3 ,4 - 2nd Methylenedioxy-benzyl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-propionyl-2 - (6 - chloro -3,4 - methylenedioxy benzyloxy) Quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - propionyl -1 - benzyl-2 - oxo-quinoline-3- - Carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6-propionyl-2 - benzyloxy-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethoxy-1 - (2 - methoxy-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethoxy-2 - (2 - methoxy-benzyloxy)-quinolin-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethoxy-1 - (3 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethoxy-2 - (3 - methoxy-benzyloxy)-quinolin-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethoxy-1 - (4 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethoxy-2 - (4 - methoxy-benzyloxy)-quinolin-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethoxy-1 - (3,4 - methylene Dioxo-benzyl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethoxy-2 - (3,4 - methylenedioxy benzyloxy) Quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethoxy-1 - (6 - chloro-3 ,4 - Methylenedioxy benzyl)-2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethoxy-2 - (6 - chloro -3,4 - methylenedioxy Benzyloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethoxy-1 - benzyl-2 - oxo- Quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethoxy-2 - benzyloxy-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (2 - methoxy-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethyl-2 - (2 - methoxy-benzyloxy)-quinoline-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (3 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethyl-2 - (3 - methoxy-benzyloxy)-quinoline-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (4 - methoxybenzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethyl-2 - (4 - methoxy-benzyloxy)-quinoline-3 - Carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (3,4 - methylenedioxy Methoxybenzyl) -2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethyl-2 - (3,4 - methylenedioxy benzyloxy) quinoline -3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - (6 - chloro-3 ,4 - Methylenedioxy benzyl)-2 - oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethyl-2 - (6 - chloro -3,4 - methylenedioxy benzyl Yloxy)-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 ,7 - dimethyl-1 - benzyl-2 - oxo-quinoline -3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-6, 7 - dimethyl-2 - benzyloxy-quinoline-3 - carboxylic acid Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl 2 - hydroxy-ethoxy-4 - methoxyphenyl 4-T-1, 2 - dihydro-6 - ethyl-1 - (2 - methoxy-benzyl) -2 - Oxo-quinoline-3 - carboxylic acid, Wherein T is 1,3 - benzo-dioxole-5 - yl 4 - methoxyphenyl 2,4 - dimethoxyphenyl 2 - benzyl oxy-4 - methoxyphenyl 2 - hydroxy - 4 - methoxyphenyl 2 - carboxy-methoxy-4 - methoxyphenyl ...
Embodiment 3
10ml 2M aqueous sodium carbonate and the 1.52g 4-anisole ylboronic acid that is in the 25ml methyl alcohol are added in the solution that is formed by 4.1g 4-(1,3-benzo dioxole-5-yl)-2-chloroquinoline-3-carboxylate methyl ester, 0.25 gram four (triphenyl phosphine) palladium (O) and 50ml toluene.In inert atmosphere, reflux and boiled 1 hour.Obtain 4-(1,3-benzo dioxole-5-yl)-2-(4-methoxyphenyl) quinoline-3-carboxylic acid methyl esters through routine operation.
Embodiment 4
Will be by the solution of 3.8g 4-(1,3-benzo dioxole-5-yl)-2-chloroquinoline-3-carboxylate methyl ester, 3.1g cesium carbonate and 40ml DMF formation and by 20ml CH 2Cl 2And 1.7g3, the solution stirring that 4-methylene-dioxy phenol forms is spent the night.Obtain 4-(1,3-benzo dioxole-5-yl)-2-(3,4-methylenedioxybenzenes oxygen base) quinoline-3-carboxylic acid methyl esters through routine operation.
Embodiment 5
Will be by 1g1,2-dihydro-1-(2, the 3-veratryl)-solution that 4-(4-methoxyphenyl)-2-oxo-6-nitroquinoline-3-carboxylic acid and 25ml methyl alcohol are formed under normal atmosphere and 20 ℃ on the 1g Raney nickel by hydrogenation to reaction terminating constantly, filter and remove solvent, obtain 6-amino-1,2-dihydro-1-(2, the 3-veratryl)-4-(4-methoxyphenyl)-2-Oxoquinoline-3-carboxylic acid.
Embodiment 6
The new distillatory acetaldehyde of 1ml is added by 6g 6-amino-1,2-dihydro-1-(2, the 3-veratryl)-solution that 4-(4-methoxyphenyl)-2-Oxoquinoline-3-carboxylic acid, 0.5g titanium tetrachloride and 100ml methyl alcohol are formed in, add 4g cyano group sodium borohydride subsequently and stirred 30 hours.Add 50% concentrated hydrochloric acid,, obtain 6-ethylamino--1,2-dihydro-1-(2, the 3-dimethoxy-benzyl)-4-(4-methoxyphenyl)-2-Oxoquinoline-3-carboxylic acid through routine operation.
Embodiment 7
5ml thionyl chloride and 1.57g phenyl-sulfamide are added by 4.85g 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-1-(3,4-(methylenedioxy) benzyl)-solution that 2-Oxoquinoline-3-carboxylic acid, 0.2g dimethylamino pyridine and 50ml pyridine are formed, stir after 10 hours, obtain 4-(1,3-benzo dioxole-5-yl)-1 through routine operation, 2-dihydro-1-(3,4-(methylenedioxy) benzyl)-2-oxygen-3-(phenyl sulfonyl-amino-carbnyl) quinoline.
Embodiment 8
Be similar to embodiment 1; make " A " and 4-(1; 3-benzo dioxole-5-yl)-1; 2-dihydro-2-oxoquinoline-3-methyl acetate is (by making 1-amino-2-(3; 4-methylene-dioxy benzoyl)-reaction of 4-phenetole and Methyl Succinyl Chloride and obtain) reaction; produce N-alkylate 4-(1; 3-benzo dioxole-5-yl)-1; 2-dihydro-1-(2-methoxybenzyl)-2-Oxoquinoline-3-methyl acetate; m.p.71-72 ℃ and O-alkylate 4-(1,3-benzo dioxole-5-yl)-2-(2-methoxy benzyloxy) quinoline-3-methyl acetate.Similarly, by " A " and 4-T-1,2-dihydro-2-oxoquinoline-3-methyl acetate, wherein T is a 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(2-methoxybenzyl)-2-Oxoquinoline-3-methyl acetate, wherein T is a 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(2-methoxyl group benzyloxy base) quinoline-3-methyl acetate, wherein T is a 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Similarly, make 3,4-(methylenedioxy) benzyl chloride and 4-T-1,2-dihydro-2-oxoquinoline-3-methyl acetate reaction, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl obtains 4-T-1,2-dihydro-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-methyl acetate, wherein T is 1,3-benzo dioxole-5-base, m.p.79-80 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-methyl acetate, wherein T is 1,3-benzo dioxole-5-base, 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl is subsequently according to the above-mentioned ester class of the mode hydrolysis that is similar to embodiment 2, obtain 4-T-1,2-dihydro-1-(2-methoxybenzyl)-2-Oxoquinoline-3-acetate, wherein T is 1,3-benzo dioxole-5-base, m.p.165-166 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl 4-T-2-(2-methoxy benzyloxy) quinoline-3-acetate, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl 4-T-1,2-dihydro-1-(3,4-(methylenedioxy) benzyl)-2-Oxoquinoline-3-acetate, wherein T is 1,3-benzo dioxole-5-base, m.p.186-187 ℃ of 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl and 4-T-2-(3,4-(methylenedioxy) benzyloxy) quinoline-3-acetate, wherein T is 1,3-benzo dioxole-5-base 4-methoxyphenyl 2,4-dimethoxy phenyl 2-benzyloxy-4-methoxyphenyl 2-hydroxyl-4-methoxyphenyl 2-carboxyl methoxyl group-4-methoxyphenyl 2-hydroxyl-oxethyl-4-p-methoxy-phenyl.
Embodiment 9
According to the mode that is similar to embodiment 2, the following ester 4-(1 of hydrolysis, 3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, m.p.210～211 ℃, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(2-methyl-benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(2, the 5-dimethoxy-benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(3,4,5-trimethoxy benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, 4-(4-methoxyphenyl)-1,2-dihydro-6-oxyethyl group-1-(2, the 5-dimethoxy-benzyl)-2-Oxoquinoline-3-carboxylic acid methyl esters, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-ethyl-1-(2, the 5-veratryl)-2-Oxoquinoline-3-carboxylic acid methyl esters, obtain following compounds 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(2-methoxybenzyl)-2-Oxoquinoline-3-carboxylic acid, m.p.250 ℃, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(2-methyl-benzyl)-2-Oxoquinoline-3-carboxylic acid, m.p.247-249 ℃, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(2, the 5-dimethoxy-benzyl)-and the 2-Oxoquinoline-3-carboxylic acid, m.p.233 ℃, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-5,6-dimethoxy-1-(3,4,5-trimethoxy benzyl)-the 2-Oxoquinoline-3-carboxylic acid, m.p.269.3 ℃, 4-(4-methoxyphenyl)-1,2-dihydro-6-oxyethyl group-1-(2, the 5-dimethoxy-benzyl)-the 2-Oxoquinoline-3-carboxylic acid, m.p.178-179 ℃, 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-ethyl-1-(2, the 5-veratryl)-and the 2-Oxoquinoline-3-carboxylic acid, m.p.199.2 ℃
The following example relates to pharmaceutical composition:
Embodiment A: phial
To be adjusted to pH=6.5 with 2N hydrochloric acid by the solution that 100g active substance I, 5g Sodium phosphate dibasic and 3I bi-distilled water are formed,, be dispersed in it in phial and freezing and sealing under aseptic condition by filter-sterilized.Each phial comprises the 5mg active substance.
Embodiment B: suppository
The mixture melt that to be made up of 20g active substance I, 100g soybean lecithin and 1400g theobroma oil and with in its impouring mould is placed cooling subsequently.Each suppository contains the 20mg active substance.
Embodiment C: solution
By 1g active substance I, 9.38g NaH 2PO 42H 2O, 28.48gNa 2HPO 412H 2O, 0.1g Zephiran chloride and 940ml bi-distilled water obtain solution.Its pH value is adjusted to 6.8, and liquor capacity is complemented to 1 liter and carry out radiation sterilization.This solution is used with the form of collyrium.
Embodiment D: ointment
500mg active substance I mixes under aseptic condition with the 99.5g vaseline.
Embodiment E: tablet
Thereby will be pressed into tablet according to traditional way by the mixture that 1kg active substance I, 4kg lactose, 1.2kg yam starch, 0.2kg talcum and 0.1kg Magnesium Stearate are formed makes every to contain the 10mg active substance.
Embodiment F: coated tablet
According to the mode compressed tablets that is similar to embodiment E, apply according to traditional way with sucrose, yam starch, talcum, tinting material and tragacanth gum coating subsequently.
Embodiment G: capsule
2kg active substance I pack into hard capsule in a usual manner so that make each capsule contain the 20mg active substance.
Embodiment H: ampoule
The solution filter-sterilized that will form by 1kg active substance I and 60l bi-distilled water and it is scattered in the ampoule freezing and sealing under aseptic condition.Contain the 10mg active substance in the per ampoule.

Claims (9)

1. compound and salt thereof shown in the formula I.
Figure A9610927900021
In the formula-Y-Z-is-NR 7-CO-,-N=C (OR 7)-or-N=CR 8R 1Be Ar, R 2Be COOR 6, (CH 2) nCOOR 6, CN, 1H-tetrazolium-5-base or CONHSO 2Ar, R 3, R 4, R 5Be R independently of one another 6, OR 6, S (O) mR 6, Hal, NO 2, NR 6R 6 ', NHCOR 6, NHSO 2R 6, OCOR 6, COR 6, COOR 6Or CN, wherein R 3With R 4Can also form O (CH jointly 2) nThe O base, R 6, R 6 'Be H, C independently of one another 1-6Alkyl, benzyl or phenyl, R 7Be (CH 2) nAr, R 8Be Ar or OAr, Ar is not for replacing or by R 9, R 10Or R 11Replace once, phenyl or the substituted naphthyl or the group of secondary or three times
Figure A9610927900022
This group be not substituted or at its phenyl moiety by R 9Or R 10Replace once or secondary, or group
Figure A9610927900023
This group be not substituted or on its cyclohexadienyl by R 9Or R 10Replace once or secondary R 9, R 10, R 11Be R independently of one another 6, OR 6, Hal, CF 3, OCF 3, OCHF 2, OCH 2F, NO 2, NR 6R 6 ', NHCOR 6, CN, NHSO 2R 6, COOR 6, COR 6, CONHSO 2Ar, O (CH 2) nR 2, O (CH 2) nOR 6Or S (O) mR 6, E is CH 2, S or O, D is carbonyl or (C (R 6R 6 ')) n, X is O or S, and Hal is F, Cl, Br or I, and m is 0,1 or 2, and n is 1,2 or 3.
2.a) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-1-(2-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid;
B) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-1-(4-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid;
C) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-1-(3,4-(methylenedioxy) benzyl)-2-oxygen quinoline-3-carboxylic acid;
D) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-1-(2-methoxybenzyl)-2-oxygen quinoline-3-acetate;
E) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-1-(3,4-(methylenedioxy) benzyl)-2-oxygen quinoline-3-acetate;
F) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-oxyethyl group-1-(2-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid;
G) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-oxyethyl group-1-(4-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid;
H) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-oxyethyl group-1-(6-chloro-3,4-(methylenedioxy) benzyl)-2-oxygen quinoline-3-carboxylic acid;
I) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro 6-oxyethyl group-1-(3,4-(methylenedioxy) benzyl)-2-oxygen quinoline-3-carboxylic acid;
J) 4-(1,3-benzo dioxole-5-yl)-1,2-dihydro-6-oxyethyl group-1-(3-methoxybenzyl)-2-oxygen quinoline-3-carboxylic acid.
3. the method for preparing Compound I according to claim 1 and salt thereof, it is characterized in that (a) for prepare wherein-Y-Z-is-NR 7-CO-or-N=C (OR 7)-Compound I, R wherein 1, R 2, R 3, R 4And R 5Compound I I as claimed in claim 1 and compound R 7-Q (III) reaction Q is the OH base of Cl, Br, I or free or reactive functional modification in formula III, R 7Such as claim 1 definition, or be (b) for prepare wherein-Y-Z-for-N=C (Ar)-Compound I, compound IV and boron compound V are reacted
Figure A9610927900042
Q is Cl, Br or I in the formula, R 1, R 2, R 3, R 4With R 5As claim 1 definition,
L in Ar-BLL ' the V formula, L ' are OH, OCH independently of one another 3, OC 2H 5Or OC 3H 7Ar such as claim 1 definition, or be c) for prepare wherein-Y-Z-for-N=C (OAr)-Compound I, making Q wherein is the compound IV and compd A r-OH (VI) reaction of Cl, Br, I or reactive functional modification OH base, and/or is that following manner is with more than one radicals R in the Compound I by way of example 1, R 2, R 3, R 4And/or R 5Be converted into more than one radicals R 1, R 2, R 3, R 4And/or R 5: being amido with nitroreduction i), is carboxyl with hydrolysis of ester group ii), iii) by the reduction amination effect amino is converted into alkylated amines, iv) carboxyl is converted into the sulfonamido carbonyl, and/or alkali or the acid of formula I is converted into one of its esters.
4, the method for pharmaceutical compositions is characterized in that one of the Compound I of claim 1 and/or its physiologically acceptable salt are converted to a kind of and at least a solid, liquid or semiliquid vehicle or the common suitable dosage forms that exists of auxiliary agent.
5. pharmaceutical composition is characterized in that containing Compound I and/or a kind of its physiologically acceptable salt of at least a claim 1.
6. Compound I and the physiologically acceptable salt thereof that are used for control disease according to claim 1.
7. as medicine and physiologically acceptable salt thereof shown in the formula I of the claim 1 of endothelin receptor antagonists.
8. the Compound I of claim 1 and/or its application of physiologically acceptable salt aspect pharmacy.
9. the Compound I of claim 1 and/or its application of physiologically acceptable salt aspect control disease.
CN 96109279 1995-08-02 1996-08-01 Endothelin receptor antagonists Pending CN1155539A (en)

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